71217-46-4

Usage

Uses

Used in Pharmaceutical Industry:
5-(Isocyanatomethyl)-1,3-benzodioxole is used as a key intermediate in the synthesis of novel naphthalimide derivatives with potent antitumor activity. These derivatives are designed to exhibit nonhematotoxic properties, which means they have minimal adverse effects on the blood-forming tissues, thus reducing the risk of side effects associated with traditional chemotherapy.
The incorporation of 5-(Isocyanatomethyl)-1,3-benzodioxole into the molecular structure of naphthalimide derivatives allows for the development of more effective and safer cancer treatments. This innovative approach to drug design has the potential to improve patient outcomes and contribute to advancements in cancer therapy.

InChI:InChI=1/C9H7NO3/c11-5-10-4-7-1-2-8-9(3-7)13-6-12-8/h1-3H,4,6H2

Upstream product

• 75-44-5 phosgene 
• 2620-50-0 1,3-benzodioxol-5-ylmethyl amine 
• 2861-28-1 1,3-benzodioxole-5-acetic acid 
• 4421-09-4 piperonylonitrile 
• 32315-10-9 bis(trichloromethyl) carbonate 

Downstream Products

• 143819-07-2 4-{1-[(Benzo[1,3]dioxol-5-ylmethyl)-carbamoyl]-3,3-diethyl-4-oxo-azetidin-2-yloxy}-benzoic acid 

Relevant academic research and scientific papers

COMPOUNDS, SALTS THEREOF AND METHODS FOR TREATMENT OF DISEASES

The present disclosure relates to compounds according to Formula (I), useful for treating diseases.

Design and Synthesis of 4-Alkylidene-β-lactams: Benzyl- and Phenethyl-carbamates as Key Fragments to Switch on Antibacterial Activity

The emergence of multidrug-resistant bacterial strains is particularly important in chronic pathologies such as cystic fibrosis (CF), in which persistent colonization and selection of resistant strains is favored by the frequent and repeated use of antibacterial agents. Staphylococcus aureus is a common pathogen in CF patients that has an associated increased multidrug resistance. In previous studies we demonstrated that the presence of a 4-alkylidene side chain directly linked to a β-lactam appeared to strengthen the potency against S. aureus, especially against methicillin-resistant S. aureus (MRSA) strains. In the present study, 21 new 4-alkylidene-β-lactams were synthesized and evaluated for antibacterial activity. We designed the new compounds to have aryl, benzyl, or phenethyl-carbamate groups on the C3 hydroxyethyl side chain. We found a correlation between biological activity and the nitrogen substituent of the carbamate group, and two phenethyl-carbamate β-lactams were shown to be valuable antibacterial agents against selected linezolid-resistant strains, with a minimum inhibitory concentrations of 2–4 mg L?1.

Organosilicon synthesis of isocyanates: II. Synthesis of aliphatic, carbocyclic, and fatty-aromatic isocyanates

Silylation of a series of aliphatic, carbocyclic, and fatty-aromatic amines gave the corresponding silyl derivatives whose yield depended on the electronic and steric structure of the substrate and the nature of the silylating agent. The yield of isocyanates obtained by phosgenation of the silyl derivatives under mild conditions decreased in going from aliphatic amines to benzylamines and rose as the length of the alkyl chain in fatty-aromatic amines extended. The most convenient procedure for the synthesis of low-boiling alkyl isocyanates was found to be based on the transformation of amines or ammonium salts into silyl or silyl silyl-carabamates, followed by pyrolysis of the latter in the presence of trichloro(phenyl)silane. Pleiades Publishing, Inc., 2006.

Inhibition of serine proteases: Activity of 1,3-diazetidine-2,4-diones

The present work demonstrates that the 1,3-diazetidine-2,4-dione nucleus is effective as a scaffold of serine protease inhibitors. Compound 1 displayed high activity against human cathepsin G and α-chymotrypsin (0.39, 0.69 nM). Compound 6 exhibited 0.85 nM inhibition of human chymase. Compound 10 was a selective inhibitor against human neutrophil elastase.

Orally Active β-Lactam Inhibitors of Leukocyte Elastase-1. Activity of 3,3-Diethyl-2-azetidinones

A thorough analysis of the mechanism of inhibition of human leukocyte elastase (HLE) by a monocyclic β-lactam and the mechanism of β-lactam hydrolysis led to the preparation of potent and highly stable inhibitors of HLE.This work led to the identification of 4--3,3-diethyl-1-carbonyl>-2-azetidinone (2) as the first orally active inhibitor of human leukocyte elastase (HLE).Analogs of 2 with different substituents on the urea N were synthesized and evaluated for their activity in vitro against HLE as well as in vivo in a hamster lung hemorrhage model.Compounds with a methyl or a methoxy group in the para position of the benzene ring were very potent in both assays.The results are discussed on the basis of the proposed model for the binding of this class of inhibitors to HLE and a possible mechanism of inhibition is presented.